


Playing Tricks

by MiladyMorningstar (PrincessPestilence)



Category: Supernatural
Genre: Alternate Universe - It's a Terrible Life, Anal Plug, Anal Sex, Bisexual Dean, Blow Jobs, Bottom Dean, M/M, Panties, Prostitution, Top Castiel, slutty dean
Language: English
Status: Completed
Published: 2016-03-23
Updated: 2016-03-23
Packaged: 2018-05-28 13:50:42
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,184
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6331681
Author URL: https://archiveofourown.org/users/PrincessPestilence/pseuds/MiladyMorningstar
Summary: <blockquote class="userstuff">
              <p>Dean likes to play games.</p><p>*</p><p>"But, then again, it's not like Dean really <em>needs</em> the money."</p>
            </blockquote>





	Playing Tricks

**Author's Note:**

  * Inspired by [Wrong Place, Right Time](https://archiveofourown.org/works/4033723) by [palominopup](https://archiveofourown.org/users/palominopup/pseuds/palominopup). 



Dean straightens the drape of his shirt; deep red and silk, half unbuttoned. It made it blatant what he was there for. He takes a draught of his light beer and twisted in the bar stool, letting his eyes rove predatorily. The bar was packed on a Friday night; men huddled intimately while others writhed and tangled on the dance floor, at the bar, up against the back wall where they thought no one would see them. Straight women weaving to and fro, wanting a taste of the gay bar scene.

 

Any other night, Dean'd walk up to them, flash them a smile and drag them back to his place for a good time. But this isn't the place for that, though. No girl comes to a gay bar to hook up with a dude. No dude comes here to pick up chicks, either. That's not what he wants tonight.

 

He catches the eye of a young blond, a couple years younger than he is, and holds his gaze meaningfully. He blatantly looks him up and down before slowly blinking his long lashes – he knows what effect they have – before turning away, sipping again at his beer. The kid'll come over if he wants to. Dean has plenty to choose from tonight.

 

He knows how to play this game.

 

In the end, the kid stays on his end of the bar, though Dean thinks he feels the stare every once in a while. His presentation does, however have its own allure, periodically drawing over men vying for his _esteemed_ company.

 

The desperate. The lonely. The _lazy_. The rich and old that no hot young thing would deign to go home with when they're too drunk to dig for gold.

 

“Hey, Sugar,” rasps some balding, middle aged executive type that Dean's familiar with; probably got a wife and a couple kids back at home in Suburbia, if the gold band 'round his finger is any indication. Definitely not what Dean wants. “How much for a night, huh?”

 

Dean scoffs, quietly. “More than you can afford, mister.”

 

Guy obviously takes offense to that. Calls Dean a stuck-up whore, said he was “just taking pity on you. You're really not as young and pretty as you think you are. Should lower your fucking standards before you end up living on the streets if you aren't already.”

 

Dean thinks he's just butthurt 'cause he couldn't land a hooker even with a pocketful of cash.

 

But, then again, it's not like Dean really _needs_ the money.

 

Mr. Married Closetcase stomps off to breathe his cigarette-breath in some other poor guy's face, and Dean turns back to his beer, raising the bottle to his lips before noticing that there's nothing there but dregs.

 

He sighs and motions for another. He's already been here longer than he'd intended and other than the twink, no one's caught his eye.

 

“He's right, ya'know,” Benny says as he passes a full bottle over. “You're too picky by half, Brother. I don't understand why you don't just get a regular boyfriend t'do this with.”

 

Dean shrugs and rolls his eyes, baring his throat as he gulps down the cold brew. “I don't have time for a relationship, Benny. And this is more fun, anyway.”

 

Benny makes a disapproving face at him, but Dean's not here for his judgement. He'd tried the dating thing – with Benny, as a matter of fact – and it just didn't give either of them what they wanted. The two of them are better off as friends, where they can hang out together on the weekends, or nights like tonight when Dean prowls the bar for new “clients”.

 

Benny knows the deal, but Dean knows from experience that other guys just don't get it; don't like the games he likes to play.

 

Dean's busy ignoring Benny's disapproval, watching the mass of dancers gyrate against one another, pulsing to the rhythm of the bass, when someone seats themselves next to him. A little older than Dean by the looks of it, but he wears it well; messy brown hair and rough stubble on a strong jaw, blue eyes that are out of this world.

 

“Can I get a Sidecar, please?” the newcomer requests in a voice that sounds like he's auditioning to play fuckin' Batman or some shit, and Dean's dick twitches at the sound.

 

Yeah.

 

This is the one.

 

Dean swivels in his seat and leans casually against the bartop as he smolders flirtatiously at the man.

 

“Hi,” he greets, voice low. “Dean. And you are?” Dean holds his hand out to shake. The stranger looks him over, no subtlety in the way he looks him up and down, licking his lips before taking Dean's proffered hand in his own. His hands are cool and dry, and-

 

“Castiel,” he responds, which. Dean's never heard that one before, but he has to say, it suits the guy.

 

“Cas-tee-ell...” Dean tries the name out, tasting it. “I like it. What's it mean?” he asks politely, drawing out the interaction.

 

“Castiel” smiles wryly, thanking Benny for the drink before turning back to Dean. “It means 'Shield of God',” he answers. “It's the name of an angel. My parents were very religious,” he adds, a self deprecating shrug indicating that his name has been the topic of many an unwanted conversation or two in his life.

 

Huh. Not an alias then, apparently.

 

“All right, then, Angel. What are you doin' out here tonight?” His question hiding a deeper meaning, but Castiel catches on quickly.

 

“I'm new to the area,” Castiel explains. “I wanted someone to help christen my new apartment, and I saw you. I'm sure someone as gorgeous as you are could have anyone you wanted, but a man can hope.”

 

It's nothing Dean hasn't heard before, but he blushes; always has had a hard time with sincerity. “Well, I gotta say, man, your odds are lookin' pretty good.” Dean grins, wetting his lips.

 

Castiel tilts his head, staring at Dean like he's looking into his soul, which is a little intimidating, but Cas must like what he sees because he throws back his Sidecar like a pro, slaps a $20 on the bar and asks “Three hundred okay?”

 

Dean's breath catches and he nods, heart racing as the game begins.

 

He follows Cas out to his car, a sleek, blue, 2013 Subaru that Dean approves of. The drive back to Castiel's apartment is tense and silent, Cas's hand sitting proprietorially on Dean's upper thigh and it's all Dean can do not to lunge across the front seat for a bit of road-head.

 

Thankfully, the ride isn't too far, and soon enough Dean's being crowded up against the wall of an elevator, Cas' mouth on his like a force of nature. The man is an inch or two shorter than Dean himself, but he clearly has no problem with the slight height difference. Dean, too, has no complaints. Instead, he tangles his fingers in Cas' messy hair and lets himself be manhandled. The elevator doors open an suddenly Cas is gone, leaving Dean bereft.

 

A whimper is torn from his throat and Castiel's brows lift, surprised, before he's dragging Dean down the hall, fumbling with the key before pushing the taller man inside. Dean has no chance to look around, Castiel's mouth back on his own, leading him blindly through the apartment until Dean falls back onto a high bed, bouncing on the firm mattress.

 

“Fuck,” the younger man swears as Castiel quickly unbuttons his white dress-shirt, not bothering to remove his tie. Dean arches his hips off the bed, digging into his back pocket for the condom and single-use packet of lube he'd stuffed in there earlier, throws them on the pillow next to him, and follows suit. He carelessly pulls his silk shirt up over his head and tosses it onto the floor – he can always have it laundered and ironed later – kicking off his shoes and shimmying off his tight jeans.

 

Castiel looks up from where he'd bent over to remove his socks and inhales sharply at the sight in front of him.

 

Dean, having undressed with quick efficiency, is laying back against Castiel's headboard, one leg bent casually, framing his crotch wrapped tantalizingly in a thin slip of hot pink lace. The tip of his cock peaks out over the low waist band, and Dean rubs the lace over his shaft, teasing himself. His legs are clean and smooth; hairless, and Castiel groans as they slide against his skin when he crawls up between them.

 

“God, you shaved,” he observes, mouthing at Dean's raised inner thigh, his voice so deep Dean can almost feel the vibrations, his skin breaking out in goosebumps.

 

Dean hums in pleasure. “Waxed, actually,” he corrects, sliding his fingers through Cas' messy hair again, pulling at the dark strands as Castiel noses up his pantyline.

 

Castiel mouths wetly at Dean's lace covered cock before continuing his way up his body, sucking at his neck and then finally licking back into his mouth. Dean allows it for a moment before exerting his strength and flipping them over, slipping down between Castiel's legs before he can complain.

 

“I've wanted to get my mouth on you all night,” he confesses, winking cheekily.

 

Castiel groans, throwing his head back helplessly. “Please.”

 

Dean chuckles darkly before tearing into the condom, cherry flavored for his pleasure. He pops the circle between his lips, and with an expert skill borne of long years of professional experience, fits the condom onto Cas' dick with his mouth, taking him to the root in one smooth motion.

 

Cas cries out, fisting his hands in the blanket, his eyes bulging as they meet Dean's twinkling back up at him in mischievous amusement.

 

“Oh, my God-!” Cas blasphemes, hips making little aborted thrusts into Dean's throat.

 

Dean hums around him, hollowing his cheeks as he slurps messily, bobbing his head a few times before he pulls off.

 

“Go ahead,” he grants, lips spit-shiny, “fuck me.”

 

His full lips wrap back around him, and Castiel obeys, one steadying hand on the back of Dean's head while his hips snap upward into Dean's throat, gag reflex long since trained out of him.

 

He fucks Dean's throat for a long few minutes before he feels the urge to cum. He holds Dean down, the younger man's nose buried in his dark pubic hair, panting heavily, but he allows Castiel to keep him there, Cas luxuriating in the wet warmth as he staves off his orgasm.

 

Finally, he pulls him off, the other man heaving for breath, face flushed and lips bruised. The older, frowns, worriedly.

 

“I'm sorry,” he apologizes, realizing he may have been too rough with the man. “Are you all right?”

 

Dean, still catching his breath, looks up at him incredulously. Instead of answering, he darts up and kisses him, roughly.

 

“Christ, don't apologize; that was fuckin' fantastic! I'm fine, believe me.” He grins and grinds his leaking cock against Castiel's, lace scratching against Cas' balls. “Feel how fine I am?”

 

Thus reassured, Cas growls, squeezing Dean's ample ass, pulling him closer. “Such a slut,” he murmurs against Dean's lips, Dean shivering at the degradation. “You like it rough?” he asks and Dean nods eagerly, nibbling Cas' upper lip. “Yeah? Are you going to let me fuck you?”

 

The younger man groans. “Fu-uck, yeah!” he agrees fervently before rolling away.

 

“Wha-” Cas starts to protest, but stops when he sees Dean slipping his panties off, flinging them toward his pile of discarded clothing, and rolling onto his stomach, pulling his knees underneath him.

 

Castiel wastes no time kneeling behind him, but he pauses at the light reflecting from between Dean's cheeks.

 

Spreading him open, he squeezes the base of his cock to keep from coming at the sight of of a pink, glass plug filling him up.

 

“Fuck.” The expletive falls from his lips. “You certainly did come prepared.”

 

Dean wriggles his ass and looks back over his shoulder. “Yup,” he pants. “You gonna take advantage of that, or what?”

 

Castiel grits his teeth at the taunt, slapping his hand against Dean's ass in retaliation. Dean grunts, the sound clearly not one of displeasure, and if Cas wasn't so wound up he'd take the time to explore that particular kink a little further, but as it is he only has a short amount of time, and he really wants to be inside Dean sometime soon.

 

Gingerly, he pulls until the plug slides out, Dean's needy hole releasing it with an obscene pop. He sets the conical toy aside, fingers slipping into the empty space, feeling him slick and warm inside, perfectly prepared.

 

“'M ready,” Dean complains, pushing back into Cas' fingers, and prostitute or not, Castiel can't deny him.

 

Grasping the other man's hips, kneeling with his knees on either side of Dean's own, he pushes inside.

 

Dean keens as Castiel slides in, burying his face in Cas' pillows, back arching as he pushes back. Together they quickly establish a quick pace, both of them too keyed up to draw it out slowly. Dean reaches underneath himself, tugging his dick to Castiel's rhythm, and Castiel briefly gives thanks to the fact that his headboard is secured to his wall, because he's sure the neighbor would have some complaints for him otherwise.

 

As it is, the room fills with the sounds of their moaning, skin slapping lewdly as Castiel drives into him, the mattress squealing under them.

 

“Fuck! Harder – c'mon, yeah, fuck me!” Dean babbles, dirty talk spilling from his lips between every growling moan and high pitched whine. Cas, in comparison is silent, sharp, panting exhales punched out with every deep thrust.

 

With anyone else, he'd be ashamed of how quickly he cums, but Dean is a professional, so Castiel can't bring himself to be embarrassed, fingers bruising Dean's hips as he bends over him, pushing in deep as he fills the condom, pumping shallowly as he milks it out of him.

 

“Yeah, yeah, yeah, yeah!” Dean chants, hand a blur beneath him as he fucks his fist, squeezing around Cas' cock as it softens inside him. Castiel leans forward, molding himself into Dean's back, reaching around to softly squeeze one of his perky nipples.

 

The extra stimulation does the trick, and Dean sobs as he comes into his palm.

 

They lay together for a moment before Castiel gets uncomfortable. He presses a kiss to Dean's freckled shoulder before tentatively pulling out, holding the condom to keep it from slipping off his softening prick.

 

Dean groans unhappily at the emptiness inside him, his free hand scrabbling for the plug. He fits the glass back inside one handed, the other cupped to contain the grossly congealing cum in his palm.

 

“Here,” he looks up and sees Castiel offering a tissue which Dean accepts with a hoarse 'thanks”.

 

The silence is awkward as they clean themselves up, Dean dressing as quickly as he'd stripped off. He attempts to pat down the wrinkles on his shirt but they're a lost cause.

 

Dean pulls out an expensive smart phone and orders a cab, and when he looks back up, Castiel is standing before him in a pair of blue, cotton, boxer-briefs and a handful of $50s.

 

“Here,” he says, offering him the cash. “You were amazing. Worth every penny. I don't suppose you have a... professional number I could call if I wanted to... procure your services again?” he asks, eyes wide, and hell, Dean almost wishes he did, if only so he didn't have to dash the guy's hopes.

 

Dean takes the money and stuffs it into his pocket, smiling apologetically. “Nah, sorry. I'll just have to see ya when I see ya, I guess. Who knows,” he shrugs, smirking, “maybe you'll get lucky.”

 

Castiel huffs a laugh and walks him to the door. He rubs the back of his neck awkwardly and Dean takes pity on him, leaning forward to press a chaste kiss to his scruffy cheek. He pulls one of the bills out of his pocket and slips it back into the waistband of Castiel's boxers.

 

“Thanks for a great night,” he says, grinning. “You earned it.” He waves and backs out of the apartment, and Castiel watches as he strolls down the hallway, only closing his door after he disappears into the elevator.

 

He hopes to run into Dean again, because he thinks he'd like to break in the kitchen table next time, make sure his apartment is well and truly christened.

 

*

 

Monday morning finds Dean at Sandover, exiting the elevator on his way to the office, only to run smack into a solid body standing in the middle of the hallway.

 

“Oof!” Dean looks down at his shirt, checking to make sure his skinny latte didn't stain his favorite tie, then up again to complain that whatever asshole should get out of the goddamn way when people are trying to walk, but quickly forgets all of that at the sight of a painfully familiar pair of shocked blue eyes.

 

“Ah, Dean! Just the man I was looking for! Dean, meet Castiel Krushnic, our new financial analyst,” Mr. Adler introduces, and – shit. “Castiel, this is Dean Winchester, our head of sales.”

 

Dean inhales bracingly before smiling beatifically at Castiel _Krushnic._ “Pleasure to meet you, Cas, welcome aboard. I'm sure we'll get along great.” If the past is any indication.

 

Castiel blinks and gives a small, if confused smile back. “The pleasure is mine, Mr. Winchester.”

 

Dean's not sure if he imagines the emphasis on his last name or not.

 

Zachariah claps them both on the shoulder. “Well, Castiel, I'm afraid I have some business to attend to. I trust that Dean will be able to help you should you need anything,” he excuses himself before disappearing into his office.

 

They watch him go before looking back at each other, Castiel taking a step back.

 

“So... Head of Sales,” the older man repeats meaningfully, and Dean can only shrug.

 

“A guy's got to get his kicks somehow,” he explains truthfully. “Figured, I could role play, or I could make some actual cash. You'll keep quiet about it, won't you? It's not exactly something I like to advertise to all my coworkers.” Though Castiel seemed like a nice guy a few days ago, Dean admits that he's nervous.

 

His fears seem to be unfounded though, as Castiel only nods. “Of course. I have no intention of sharing the experience, so to speak,” he quirks a wry smile that Dean shares. “You were right though,” he says, and Dean tilts his head, confused.

 

“About 'seeing me when you see me',” he explains, relaying Dean's parting quote back to him.

 

Dean laughs, shaking his head in disbelief. “Yeah, I guess I was,” he agrees.

 

“So how's my luck, then?” Cas asks teasingly, provokingly.

 

The taller man stares contemplatively, taking in Castiel's pristine work clothes and name tag along with his flirtatiously sincere expression. His eyes dart down the hall to Adler's office before back to Castiel.

 

“We'll have to find out, won't we?”

 

**Author's Note:**

> [Dean's Panties](https://s-media-cache-ak0.pinimg.com/736x/cb/4a/0d/cb4a0d51b6b10a7280f5d8af4db02990.jpg) \- not the top, just the underwear.  
> [Dean's Plug](http://g04.a.alicdn.com/kf/HTB13kXLLXXXXXXPXVXXq6xXFXXXm/BIG-PINK-Crystal-glass-anal-dildos-anal-font-b-plug-b-font-sex-products-butt-font.jpg)


End file.
